08/18/2025

Five Tips for Approaching Difficult Conversations at Work

Handle these conversations with honesty, empathy and clarity

A handful of community leaders approached me about halfway through my first year as a school leader. Some teachers — particularly the tenured vets — were concerned with certain aspects of my leadership style and were starting to vent to board members and other people of influence. After hearing these people out, I asked them what most people in a similar situation would want to know. "Why aren’t they coming to me with this?" I was told that they were afraid of losing their jobs. 

Soon after those conversations, I invited two veteran teachers to my office. My goal was to better understand the faculty’s concerns and what I could do to address them. These two women had both been on staff for years and were well-connected and respected internally. I felt that they were likely to have valuable information and insights to share. 

As I sat across the table from them and explained my intentions, they looked at me studiously. When I finished, both exhaled deeply, and one even laughed that uncomfortable kind of laugh that we use when we are released from a subdued fear. When I asked for clarification, I was told straight out that they had feared the worst for themselves before entering my office. My words had helped put them at ease. 

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